3 Answers
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Poor in spirit means that you feel you have no moral riches and are in need. You feel you need 'spiritual' life. 'Poor' (πτωχός) used in this verse means 'reduced to being a beggar'. This makes sense and we can confirm its meaning by comparing other statements of Jesus, for he often said the same things in many ways.

One good match that seems to bring light to the phrase is:

When the teachers of the law who were Pharisees saw him eating with the sinners and tax collectors, they asked his disciples: “Why does he eat with tax collectors and sinners?” On hearing this, Jesus said to them, “It is not the healthy who need a doctor, but the sick. I have not come to call the righteous, but sinners.” (NIV Mark 2:16-17)

Those who feel they are sinful or 'morally sick' and so cry out to Jesus to be saved, are 'poor in spirit' thus they are the ones and only ones that inherit God's kingdom. Those who are self righteous are morally confidant and rich, these Jesus can not save.

This makes sense that Jesus would make this the first attitude of a Christian because it is by being poor in spirit or 'reduced to being a beggar'. That you actually 'begin' the Christian life with this explains why it is the first be-attitude. It also fits and explains the second attitude of mourning which is the other side of the same coin. It naturally follows for a Christian once recognizing his poverty due to sin, he will mourn on account of it.

God will make happy, or 'bless' such people with inexpressible spiritual riches and joy. This is the core message of the gospel.

I am not sure that the core message of the gospel is to bring happiness.
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ioSamuraiAug 7 '12 at 15:03

@libertas: We have to be careful about the way it's phrased, but John Piper makes a strong case for that position. Welcome to Biblical Hermeneutics, by the way.
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Jon Ericson♦Aug 7 '12 at 20:56

@JonEricson Thanks for the welcome, I think that happiness is something that can come and go on this earth, joy of course is a fruit of the Spirit. But the core message of the gospel, that is, the ultimate cosmic purpose, is the marriage of Christ and the Church after the destruction of earth, happiness will be there for sure, but it's far from the main point.
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ioSamuraiAug 7 '12 at 21:11

@libertas: If you'd like to continue this conversation, let's do it in The Library. (I don't mean to cut the discussion off, but it's getting off-topic. ;-)
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Jon Ericson♦Aug 7 '12 at 22:08

Perhaps, more accurately, the poor in spirit are the two sides of the same coin. The apparent duality of particle and wave properties of a photon even though they are but a singularity. The seeming duality of works vs faith, even though they are but a singularity in phenomenon.

Will this perception of mutual predisposition descend into arguments of predestination. It should not. They are the spontaneous rewards and consequences of each other. Just like saying "bright is the sunlight". It's an observation.

Diogenes' apparent perception that Civilisation's pomposity is a degenerative trait. Pomposity has no useful function to the purpose and existence of the human race. Pomposity unnecessarily consumes resources that could otherwise further fuel the progress of the human race. One should deny oneself the unnecessary luxuries and rituals in order to attain progress.

If you see someone in need, provide help. If you see someone's feet smelling wash them - don't wait for a ritual to begin, don't wait for a special holiday to do it. If you see a package fallen off the supermarket shelf, pick it up and put it back onto the shelf. Don't wait for the supermarket associate to have to do it themselves.

But, I'm afraid that some unfortunate souls may have turned the washing of feet into a pompous ritual.

For theirs is the kingdom of heaven.

People who have found singularity in being poor in spirit and being blissful, who have found the singularity of having faith and exhibiting works have already created the kingdom of heaven.

As Alexander the Great supposedly said, that if he were not Alexander he would be Diogenes. Apparently, Alexander knew that Diogenes was blissful in the heaven that he demonstrated in his style of living to the people around him, that they too could create to find the true happiness within themselves.

Diogenes denying himself of unneccesary luxuries and unneccesary burdens of so-called "civilization" to eliminate the clutter in one's life, to be able to enjoy the core values of life and be blissful. And found the kingdom of heaven therewith.

Being poor in spirit affords oneself the neglect of expectations from neighbours and friends or strangers, allowing the freedom to pursue one's course of life unhindered - and that is bliss.

The argument of predestination is a skewed view due to a misaligned perception of predisposition. Predestination's validity depends on the concept of temporal sequence and consequence. If time did not exist or existed in another way, the Calvinist would never have perceive the unneccesary concept of predestination. The term "predispostion" would be replaced by the term "mutual disposition".

The perception of time is due to the 2nd law of Thermodynamics. That our perception of consequentiality must progress in the path of increasing entropy. Throw away all the unneccesary burdens of "civilization", and then justce will flow as a naturally flowing stream as time flows towards increasing entropy. And then you will clearly see the interplay and balance between the potential energy of faith with the kinetic energy of work. And then you would not have to worry if either works or faith is a predestined path towards heaven.

And you would realise that one asymptotic day the increase of entropy will come to a rest - at which point you will achieve the nirvana of Sabbath and you will see your Creator. And being meek is to dispense away with non-necessities and non-essentials, like clouds blocking your view of the stars, to allow you to look at that point in "time" straight into the face of your Creator.

Blissful are the peacemakers, theirs is the enjoyment of the land wherein they dwell.

The whole beatitudes is a singularity of mutual natural response blissfulness and an existence of heaven. Not of any mono-directional vectors of consequentiality. But a whole continuum where each verse is but an intrapolative dot of a sphere. Undeterred by the consequence of time.

Perhaps, my explanation is a little pompous but I feel the allegories were essential.

Yes, it is those people who do not mistake material wealth (kinghood) for spiritual wealth (priesthood). Priestly obedience must always come first (Abel before Cain). We believe (as obedient, priestly servants), and then we understand (as kingly sons).

"For you say, I am rich, I have prospered, and I need nothing, not realizing that you are wretched, pitiable, poor, ublind, and naked. I counsel you to buy from me gold refined by fire, so that you may be rich, and wwhite garments so that you may clothe yourself and the shame of your nakedness may not be seen, and salve to anoint your eyes, uso that you may see." Rev 3.